Dimethylformamide → 3-(Difluoromethoxy)benzaldehyde

HRID 1042629Notes

Reaction equation

HRID 1042629 reaction equation
[O:1]=[C:2]1[CH:7]=[C:6]([CH:8]=[O:9])[CH:5]=[CH:4]N1.Cl[C:11]([F:16])([F:15])C([O-])=O.[Na+].[CH3:18]N(C=O)C>C(#N)C.C(OCC)(=O)C>[F:15][CH:11]([F:16])[O:1][C:2]1[CH:7]=[C:6]([CH:5]=[CH:4][CH:18]=1)[CH:8]=[O:9]

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 15126692-Hydroxy-4-pyridinecarboxaldehydeHCID 2734985Sodium chlorodifluoroacetate

Product 1

HCID 27369853-(Difluoromethoxy)benzaldehyde

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 2-oxo-1,2-dihydropyridine-4-carbaldehyde (1.72 g, 11.3 mmol) in 25 mL of acetonitrile was added sodium chlorodifluoroacetate (0.925 g, 7.51 mmol). The reaction was heated to reflux under an atmosphere of nitrogen for 15 h, and then DMF (3 mL) was added. The mixture was heated to 100° C. for 3 d, cooled to rt, and diluted with ethyl acetate. The organic solution was washed with brine, dried over sodium sulfate, filtered, and concentrated in vacuo to provide 3-(difluoromethoxy)benzaldehyde.

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux under an atmosphere of nitrogen for 15 h
  3. temperaturecooled to rt
  4. washThe organic solution was washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-de68ac8e0ea145089587f8be7584033d
Source dataset
uspto-grants-2013_10
Patent number
US08557992B2

Reaction notes

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